title: Distinct chemoselectivities in the platinum-catalyzed 1,2-carboalkoxylations of 5-alkoxypent-1-yn-3-ol derivatives.
abstract: Two distinct Pt-catalyzed carboalkoxylations of alkynes are reported. The cycloisomerization of 5-alkoxypent-1-yn-3-ol derivatives 5 produces 2,6-dioxabicyclo[3.1.0]hexanes 6; the mechanism is postulated to involve a hydroxyl-triggered [3.3]-sigmatropic allyl rearrangement. As the same catalysis is extensible to their tertiary alcohol analogues 7, distinct dihydrofuranyl alcohols 8 were obtained through a [3.3]-allyl rearrangement that is not assisted by the hydroxyl group.
authors.affiliation: Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, People's Republic of China.
authors.forename: Chun-Ming
authors.initials: CM
authors.lastname: Ting
authors.forename: Chiou-Dong
authors.initials: CD
authors.lastname: Wang
authors.forename: Rupsha
authors.initials: R
authors.lastname: Chaudhuri
authors.forename: Rai-Shung
authors.initials: RS
authors.lastname: Liu